Dimethylamine, hydrochloride → HCID 89610459, compound

HRID 1507690Notes

Reaction equation

HRID 1507690 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:10]=1[C:35]([O-])=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:38]([NH+:40](CC)[CH2:41]C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CNC.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:15]([O:14][C:13]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([C:35](=[O:36])[N:40]([CH3:41])[CH3:38])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:12]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89610545HCID 89610545, compound

Product 1

HCID 89610459HCID 89610459, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of triethylammonium 3,4-bis(benzyloxy)-5-(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (5) (10.84 g, 17.99 mmol) in DMF (150 mL), at 0° C. was added HATU (10.26 g, 27.0 mmol), dimethylamine hydrochloride (2.93 g, 36.0 mmol) and DIPEA (18.8 ml, 108 mmol). The reaction mixture was stirred at RT for 16 h and partitioned between EtOAc (500 mL) and 1M HCl (aq.) (250 mL). The organic phase was washed successively with 1M HCl (aq.) (250 mL), sat. NaHCO3 (aq.) (2×250 mL), and brine (2×250 mL), dried (MgSO4), filtered and concentrated in vacuo to afford ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (6) (7.62 g, 79%) as a light yellow oil, that solidified on standing: m/z 529 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.51-7.21 (m, 10H), 7.14-7.03 (m, 2H), 6.94-6.84 (m, 2H), 5.12 (s, 2H), 4.96 (s, 2H), 4.00 (q, J=7.1 Hz, 2H), 3.77 (s, 3H), 2.70 (s, 6H), 1.00 (t, J=7.1 Hz, 6H).

Workup

  1. custompartitioned between EtOAc (500 mL) and 1M HCl (aq.) (250 mL)
  2. washThe organic phase was washed successively with 1M HCl (aq.) (250 mL), sat. NaHCO3 (aq.) (2×250 mL), and brine (2×250 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e4804d0a087441dab8bf1a25501b3ed
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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